What to bring
To ensure a comfortable and enjoyable sailing experience, we recommend bringing a few essentials — though we also provide them for your convenience.
Sunscreen & Sunglasses
Protect yourself from the sun while enjoying the open waters.
Light Jacket or Windbreaker
The breeze can get cool, especially in the evening.
Non-Slip Footwear
Comfortable, flat shoes with good grip for stability on deck.
Camera or Smartphone
Capture breathtaking moments and scenic views.
Personal Essentials
Any medications, seasickness remedies, or special items you may need.
Refreshments
Bring bottled water, soft drinks, or your favorite beverages to stay hydrated. Light snacks like fruits or sandwiches are great for the trip.
Capacity
Our sailing vessel is designed to provide a spacious and intimate experience:
Maximum Guests
Our capacity is six maximum guests.
Ideal for:
Small gatherings, private cruises, and special events.
For larger groups or special requests, contact us to discuss custom arrangements.
Weather
Sailing is a weather-dependent experience, and we prioritize safety and comfort.
- We monitor conditions closely and will notify guests in advance of any schedule changes.
- In case of severe weather, we offer rescheduling or alternative arrangements.
- Light rain? We can still sail! The experience remains enjoyable unless conditions become unsafe.
Accommodations
Step aboard and enjoy a comfortable sailing experience designed with relaxation and convenience in mind. Our sailboat offers:
Spacious Deck Area
Perfect for taking in the views, socializing, or simply relaxing as you glide across the water.
Covered Cockpit with Clear Panels
Stay protected from wind and light rain while still enjoying panoramic scenery.
Comfortable Seating
Cushioned seating in the cockpit ensures a cozy and enjoyable experience for all guests.
Onboard Restroom
A convenient marine-style restroom is available for your comfort.
Safety Features
Equipped with secure rigging, fenders, and well-maintained features to ensure a smooth and safe journey.
Whether you’re looking for a relaxing day cruise, a romantic sunset sail, or a private celebration, our boat provides the perfect balance of comfort and adventure.
Stories from the Sea
Real adventures, real smiles — hear from those who made waves with us.
Steffanie GerkinTrustindex verifies that the original source of the review is Google. Had an amazing time on this stunning sailboat, will definitely be back to do this again! john hallTrustindex verifies that the original source of the review is Google. We had a fantastic time sailing with Captain Matt in Lake Michigan from the shore of Milwaukee, WI. Recommended! Sean RyanTrustindex verifies that the original source of the review is Google. Had a fantastic sunset cruise with Captain Matt. He was ready to go and we started on time and went a little bit long. Matt made sure we were safe, made the best of light wind and was engaging the entire time. I highly recommend! J Andrew GearyTrustindex verifies that the original source of the review is Google. Excellent! I booked a sunset sailing trip with my family for our Milwaukee vacation. The communication setting up the trip was clear and the captain was responsive. The directions on where to go and what to prepare for were clear and very useful. We had an amazing time on the sailing trip! It was a beautiful night and the crew was great. The captain and his crewmate treated us very well and were a lot of fun to chat with during the voyage. I would not hesitate to recommend or even book another trip with Sea Dog Sailing. Thank you for a wonderful experience! Rachel MacGregorTrustindex verifies that the original source of the review is Google. This was the BEST experience, I could not recommend it enough! I came to visit my sister in Milwaukee after she moved here and decided to try this because it sounded fun but it was by far our favorite thing from my entire visit (and I work in the travel industry so I am great at finding lots of fun things to do). Captain Bob was fantastic, so knowledgable about sailing and the lake and city, plus we got to try steering some which was really cool! Joseph FasiTrustindex verifies that the original source of the review is Google. Magical and fun. Captain Bob was the best host and made the day spectacular. I have lived in Milwaukee for many years and have never savored the view of the skyline as we did from 5 miles out in Lake Michigan on a beautiful sunny day. He answered my incessant questions with patience and knowledge. I look forward to another charter with Sea Dog Sailing. the one down side— Now I have what may be a burning desire for a sail boat of my own! Noah HunterTrustindex verifies that the original source of the review is Google. Capt. Robert and his crew were so welcoming as soon as you walk down to the boat. If you have never been sailing you absolutely have to book a trip with this crew. My wife and I have never been and they made an amazing trip for both of us, explaining what they were doing with lines and sails, telling us how things work with the lake and sailing, and overall making us feel as comfortable and safe as possible. The boat is a beautiful vessel, the only downside was we wished we could’ve stayed and sailed longer! So if you’re in Milwaukee and want to experience something fun and exciting with a expert captain and friendly crew, book a trip with sea dog sailing! Scott HartmanTrustindex verifies that the original source of the review is Google. Had a great time sailing with Captain Bob and his crew. 5 stars, would recommend!